US4433010A - Process for preparing glass constructions - Google Patents

Process for preparing glass constructions Download PDF

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US4433010A
US4433010A US06/454,520 US45452082A US4433010A US 4433010 A US4433010 A US 4433010A US 45452082 A US45452082 A US 45452082A US 4433010 A US4433010 A US 4433010A
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polyol
weight
component
glass
materials
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Josef Pedain
Wolfgang Wellner
Klaus Konig
Hermann Gruber
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Bayer AG
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Bayer AG
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Assigned to BAYER AKTIENGESELLSCHAFT, A CORP. OF GERMANY reassignment BAYER AKTIENGESELLSCHAFT, A CORP. OF GERMANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: GRUBER, HERMANN, KONIG, KLAUS, PEDAIN, JOSEF, WELLNER, WOLFGANG
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/088—Removal of water or carbon dioxide from the reaction mixture or reaction components
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C09K3/1021—Polyurethanes or derivatives thereof
    • E—FIXED CONSTRUCTIONS
    • E06—DOORS, WINDOWS, SHUTTERS, OR ROLLER BLINDS IN GENERAL; LADDERS
    • E06B—FIXED OR MOVABLE CLOSURES FOR OPENINGS IN BUILDINGS, VEHICLES, FENCES OR LIKE ENCLOSURES IN GENERAL, e.g. DOORS, WINDOWS, BLINDS, GATES
    • E06B3/00—Window sashes, door leaves, or like elements for closing wall or like openings; Layout of fixed or moving closures, e.g. windows in wall or like openings; Features of rigidly-mounted outer frames relating to the mounting of wing frames
    • E06B3/66—Units comprising two or more parallel glass or like panes permanently secured together
    • E06B3/663—Elements for spacing panes
    • E06B3/66309—Section members positioned at the edges of the glazing unit
    • E06B3/66342—Section members positioned at the edges of the glazing unit characterised by their sealed connection to the panes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2190/00—Compositions for sealing or packing joints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
    • C09K2200/0652—Polyisocyanates

Definitions

  • This invention relates to novel one-component or multi-component systems which are resistant to hydrolysis, based on organic polyisocyanates and selected polyhydroxyl compounds, for use as or for the preparation of composite materials which are resistant to chemicals and UV light for glass constructions.
  • the present invention relates to the preparation of glass constructions comprising applying, to glass, a composition comprising a polyisocyanate component comprising at least one organic polyisocyanate and a polyol component, said polyisocyanate and total polyol component being present in quantities corresponding to an isocyanate index of from 80 to 130, and optionally, known auxiliary agents and additives.
  • the polyol component comprises at least one dihydroxy polyester carbonate with a molecular weight of from 800 to 3000, comprising a reaction product of hexanediol-(1,6) with ⁇ -caprolactone and/or ⁇ -hydroxycaproic acid (in a molar ratio of hexanediol-(1,6): ⁇ -caprolactone and/or ⁇ -hydroxycaproic acid within the range of 4:1 to 1:3), and diaryl carbonates, optionally present as a mixture with up to 40% by weight, based on the total quantity of the component, of other polyols with molecular weights of from 62 to 4000, optionally containing ester groups.
  • the present invention also relates to the preparation of glass constructions comprising applying, to glass, a composition comprising an isocyanate prepolymer which has been obtained by the reaction of said polyol component with excess quantities of said polyisocyanate component, and which is optionally present as a mixture with up to about 30% by weight, based on the prepolymer, of organic polyisocyanates other than the polyisocyanate or polyisocyanates used for its preparation, and optionally up to a total of 30%, by weight, based on said isocyanate prepolymer, of diprimary aromatic diamines within the molecular weight range of from 108-400 and/or of chain-lengthening agents carrying two blocked amino groups which may be activated by moisture, said chain-lengthening agents being selected from the group consisting of bis-aldimines, bis-ketimines, bis-enamines and bis-oxazolidines, and optionally other known auxiliary agents and additives.
  • the polyisocyanate component according to the invention comprises at least one organic polyisocyanate of the type known in polyurethane chemistry, such as compounds corresponding to the formula:
  • Q denotes an aromatic hydrocarbon group with a total of 6 to 15 carbon atoms, optionally methyl-substituted or containing methylene bridges, an aliphatic hydrocarbon group having 4 to 18, preferably 6 to 10, carbon atoms, a cycloaliphatic hydrocarbon group having 6 to 15 carbon atoms, or a xylylene group, and
  • n denotes an integer from 2 to 5, preferably 2.
  • Examles of polyisocyanates suitable for purposes of the invention include tetramethylene diisocyanate, hexamethylene diisocyanate, 1,12-dodecane diisocyanate, cyclohexane-1,3- and -1,4-diisocyanate and any mixtures of these isomers, 1-isocyanato-3,3,5-trimethyl-5-isocyanato-methylcyclohexane (IPDI), perhydro-2,4'- and/or 4,4'-diphenyl methane diisocyanate.
  • IPDI 1-isocyanato-3,3,5-trimethyl-5-isocyanato-methylcyclohexane
  • Additional examples include 1,3- and 1,4-phenylene diisocyanate, 2,4- and 2,6-tolylene diisocyanate and any mixtures of these isomers, diphenylmethane-2,4'- and/or 4,4'-diisocyanate, 3,2'- and/or 3,4'-diisocyanato-4-methyldiphenylmethane, naphthylene-1,5-diisocyanate, triphenylmethane-4,4',4"-triisocyanate, polyphenyl-polymethylene polyisocyanates, such as are obtainable by aniline-formaldehyde condensation followed by phosgenation, as described, for example, in British Pat. Nos.
  • Polyisocyanates containing carbodiimide groups as described in German Pat. No. 1,092,007, polyisocyanates containing allophanate groups, as described, for example, in British Pat. No. 994,890 and Belgium Pat. No. 761,626, polyisocyanates containing isocyanurate groups as described, for example, in U.S. Pat. No. 4,288,586, German Pat. Nos. 1,022,789, 1,222,067 and 1,027,394, German Offenlegungsschriften Nos. 1,929,034, 2,004,048 and 2,839,133 or in European Patent Specification No. 10,589 may also be used.
  • Still further examples include polyisocyanates containing urethane groups, as described, for example, in Belgium Pat. No. 752,261 or in U.S. Pat. No. 3,394,164, polyisocyanates containing acrylated urea groups, according to German Pat. No. 1,230,778 and polyisocyanates containing biuret groups, as described, for example, in German Pat. No. 1,101,394, British Pat. No. 889,050 and French Pat. No. 7,017,514.
  • Preferred polyisocyanates for use according to the invention include IPDI, 4,4'-diisocyanato-dicyclohexylmethane, tris-(isocyanatohexyl)-biuret, optionally mixed with its higher homologues, as described, for example, in German Pat. No. 1,101,394, tris-(isocyanatohexyl)-isocyanurate, optionally mixed with its higher homologues, as described, for example, in European Patent Specification No.
  • 4,4'-diisocyanatodiphenylmethane and mixtures thereof with 2,4'-diisocyanatodiphenylmethane, and/or its higher homologues i.e., the known phosgenation products of aniline/formaldehyde condensates.
  • Derivatives of 4,4'-diisocyanatodiphenylmethane, which have been modified, i.e., liquefied, by partial carbodiimidization of the isocyanate groups or by partial urethanization of the isocyanate groups, by a reaction with polypropylene glycols, having a maximum molecular weight of 700, are also particularly suitable for use according to the invention.
  • mixtures of these polyisocyanates may also be used according to the invention.
  • the total polyol component according to the invention comprises dihydroxypolyester carbonates with molecular weights of from 800 to 3000, preferably of from 1500 to 2500, calculated from the hydroxyl group content.
  • dihydroxypolyester carbonates are reaction products of hexanediol-(1,6) with ⁇ -caprolactone and/or ⁇ -hydroxycaproic acid, in a molar ratio of hexanediol-(1,6) to ⁇ -caprolactone and/or ⁇ -hydroxycaproic acid in the range of 4:1 to 1:3, preferably 2:1 to 1:2, and most preferably 1.2:1 to 1:1.2, and diarylcarbonates.
  • the preparation of such dihydroxy polycarbonates is carried out by known methods (see, Houben-Weyl, XIV/2, page 48) and has been described, for example, in U.S. Pat. No. 3,640,967.
  • hexanediol-(1,6) is first reacted with ⁇ -caprolactone (with ring opening) and/or with ⁇ -hydroxycaproic acid (with the elimination of water) to form an ester glycol.
  • This ester glycol is reacted with sub-equivalent quantities of diaryl carbonate to be converted, by heat, into the corresponding polyester-polycarbonate, containing OH end groups, with the elimination and removal of the corresponding phenol compound.
  • the diaryl carbonate used for the preparation of the polyols, used in the process according to the invention may be diphenyl carbonate, dinaphthyl carbonate, dicresyl carbonate or the like.
  • the total polyol component which is essential to the invention may contain, in addition to the above-mentioned dihydroxy polyester carbonates, up to 40%, preferably up to 20%, by weight, of other polyhydroxyl compounds having aliphatically-bound hydroxyl groups, and optionally containing ester groups. These polyhydroxyl compounds have a calculated molecular weight of from 62 to 4000, preferably of from 800 to 3000.
  • polyester polyols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycols, hexylene glycols, trimethylolpropane or glycerol or polyester polyols, within the specified molecular weight range, which may be synthesized, for example, from the above-mentioned low molecular weight polyols and polycarboxylic acids.
  • polyesters of hexanediol-(1,6) and adipic acid or polycaprolactones which are obtained by ring-opening esterification of ⁇ -caprolactone, or by the elimination of water from ⁇ -hydroxycaproic acid, are particularly preferred.
  • isocyanate index the number of isocyanate groups present in the mixture per 100 isocyanate-reactive groups (e.g., hydroxyl groups)).
  • These mixtures may be used as sealing materials, without the addition of any further auxiliary agents or additives, or they may be used together with further auxiliary agents and additives.
  • These optional auxiliary agents and additives may be added either to the mixtures of the components or to the individual components before they are mixed.
  • auxiliary agents and additives used include, for example, solvents, e.g., ethyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, ethylene glycol-monoethyl ether-acetate, toluene, xylene, petroleum spirit or any mixtures of these solvents.
  • solvents e.g., ethyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, ethylene glycol-monoethyl ether-acetate, toluene, xylene, petroleum spirit or any mixtures of these solvents.
  • the process according to the invention is preferably carried out solvent-free or with the use of only small quantities of solvent.
  • the solvents may be used in a quantity of up to 40% by weight, preferably up to 20% by weight, based on the quantity of sealing material.
  • auxiliary agents and additives include, for example, plasticizers, such as tricresyl phosphate, phthalic acid diesters or chloroparaffins; pigments and fillers, such as titanium oxide, barium sulfate, chalk and carbon black; catalysts, such as N,N-dimethylbenzylamine, N-methylmorpholine, lead octoate or dibutyl tin dilaurate; leveling agents; thickeners; stabilizers, such as substituted phenols; or bonding auxiliaries, such as organo functional silanes.
  • plasticizers such as tricresyl phosphate, phthalic acid diesters or chloroparaffins
  • pigments and fillers such as titanium oxide, barium sulfate, chalk and carbon black
  • catalysts such as N,N-dimethylbenzylamine, N-methylmorpholine, lead octoate or dibutyl tin dilaurate
  • leveling agents such as thickeners;
  • the moisture adhering to the fillers and pigments may be removed by preliminary drying or by the addition of water-absorbent substances, such as, for example, molecular sieve zeolites.
  • a prepolymer containing isocyanate groups is prepared in a first reaction step by the reaction of the polyisocyanate and total polyol described above.
  • This reaction is carried out in a known manner, observing an isocyanate index of from 150 to 1,500, preferably of from 200 to 400, or by the reaction of the total polyol component with a large excess of the polyisocyanate component followed by the removal, optionally by distillation, of at least part of the unreacted excess of the polyisocyanate component.
  • the resulting prepolymer containing isocyanate groups is used either alone, or in admixture with up to about 30% by weight, based on the prepolymer, of polyisocyanates of the type exemplified above which are different from the polyisocyanate used for the preparation of the prepolymer.
  • the prepolymer component according to the invention thus consists of the above-mentioned isocyanate prepolymers or of mixtures thereof with other polyisocyanates of the type exemplified. It may be used as a moisture-hardening sealing material, either alone, or with the addition of the auxiliary agents and additives exemplified above.
  • the prepolymer component is mixed with the diamine component according to the invention before it is used.
  • This diamine component comprises diprimary aromatic diamines in the molecular weight range of from 108 to 400 and/or blocked diamine chain-lengthening agents which are activated by moisture.
  • diprimary aromatic diamines examples include p-phenylene diamine, 2,4- and/or 2,6-diamino toluene and 2,4'- and/or 4,4'-diaminodiphenylmethane, but they are preferably diprimary aromatic diamines, which have at least one alkyl substituent with 2 to 3 carbon atoms in an ortho-position to each amino group, and optionally also methyl substituents in other positions ortho to the amino groups.
  • Typical examples of such preferred aromatic diamines include 1-methyl-3,5-diethyl-2,4-diaminobenzene, 1-methyl-3,5-diethyl-2,6-diaminobenzene, 1,3,5-triethyl-2,6-diaminobenzene, 3,5,3',5'-tetraethyl-4,4'-diaminodiphenylmethane, 3,5,3',5'-tetraisopropyl-4,4'-diaminodiphenylmethane, 3,5-diethyl-3',5'-diisopropyl-4,4'-diaminodiphenylmethane and any mixtures of such diamines.
  • the blocked diamine chain-lengthening agents include bis-oxazolidines of the type described, for example, in U.S. Pat. Nos. 3,661,923, 3,864,335 and 3,743,626 and, in particular, U.S. Pat. No. 4,002,601; or bis-aldimines, bis-ketimines or bis-enamines of the type described, for example, in German Auslegeschrift No. 1,520,139, German Offenlegungsschrift No. 2,125,247 or U.S. Pat. Nos. 3,267,078 or 3,715,338.
  • Suitable blocked diamines generally have a molecular weight of from 196 to 600.
  • the diamine component is preferably added to the isocyanate prepolymers in quantities of from 1 to 30%, preferably from 5 to 25%, by weight, based on the prepolymer component.
  • the blocked diamine chain-lengthening agents mentioned as examples are most preferably used as the sole diamine component.
  • the resulting mixtures of the prepolymer and diamine components may also be used as sealing materials according to the invention, either with or without addition of the auxiliary agents and additives exemplified above.
  • These sealing materials are mainly moisture-hardening materials, unless the diamine component contains a sufficient quantity of free diamines for hardening.
  • the process according to the invention is carried out according to the first or the second embodiment.
  • the only essential factor is that the sealing material should contain the dihydroxypolyester carbonates which are an essential feature of the invention.
  • the above-described range of variations of the process according to the invention does, however, enable the mechanical properties of the hardened sealing compounds finally obtained to be easily adjusted.
  • hardening of the composite materials does, of course, depend upon the presence of atmospheric moisture. In the absence of atmospheric moisture, only the first embodiment should be used.
  • the composite materials according to the invention are eminently-suitable for the sealing of glass constructions, in particular, in the manufacture of insulating glass panes.
  • Insulating glass consists of two or more panes held together at a desired distance by a hollow section, for example, of metal.
  • the panes and the section form an external joint into which the sealing material according to the invention is introduced, in a liquid or plastic form, and it then hardens within 1 to 48 hours, depending upon the chemical composition and catalysis. The whole construction is then held together by the sealing material.
  • the sealing material must satisfy stringent requirements as regards its mechanical and other properties.
  • the sealing materials according to the invention ideally fulfill these requirements.
  • the adherence between the glass pane and the joint is very good and undergoes virtually no change in the course of ageing and on exposure to light.
  • the permeability to water vapor is so slight that the thaw point of the unit does not rise even after prolonged exposure to moisture.
  • One characteristic which is particularly advantageous is that the sealing materials according to the invention retain their plasticity and elasticity even at low temperatures.
  • the composite materials according to the invention are also suitable for the manufacture of any type of glazing, for example, for the construction of automobiles, aircraft, railway coaches or buildings.
  • a liquid polyester polycarbonate prepared from hexanediol-(1,6), ⁇ -caprolactone and diphenyl carbonate, using these reactants in a molar ratio of 7,85:7,85:6,85 (average molecular weight about 2000, OH number 56),
  • Polyether of propylene oxide started on propylene glycol (average molecular weight about 2000, OH number 56).
  • Liquid polyester of adipic acid, butandeiol-(1,4), ethanediol and diethylene glycol (OH number 56, average molecular weight about 2000).
  • This example illustrates the high resistance to weathering of solvent-free, white sealing compound.
  • Polyol B 100 parts are ground up with 50 parts of titanium dioxide (of the rutile type) and 5 parts of zeolite powder in a ball mill. The resulting substance is then mixed with 20 parts of a solvent-free polyisocyanate which consists of a monomer-free biuret adduct of about 3 mol of hexamethylene diisocyanate and which has a viscosity of 10,000 mPa at 25° C., and an isocyanate content of 21.9%.
  • a solvent-free polyisocyanate which consists of a monomer-free biuret adduct of about 3 mol of hexamethylene diisocyanate and which has a viscosity of 10,000 mPa at 25° C., and an isocyanate content of 21.9%.
  • the compound is used to coat a glass panel measuring 30 ⁇ 15 cm by pouring the compound on the panels. Smooth coatings forming bubble-free layers about 0.5 mm thick, which have a Shore A hardness of 75, are obtained after hardening. After the panels have been exposed to weathering outdoors for one year in a Florida climate, the surfaces of the panels show a slight loss of gloss but no discoloration, cracks or crazing.
  • Example 1 is repeated but using Polyol C instead of Polyol B.
  • the coating After outdoor weathering for a year in a Florida climate, the coating is again found not to be discolored, but the surface shows severe signs of chalking and is cracked and heavily crazed and has partly become detached.
  • This example illustrates the preparation of a low-solvent composite material capable of being hardened by moisture, which is suitable for the constructional sealing of windscreens in the manufacture of automobiles.
  • An isocyanate prepolymer having an isocyanate content of 4.1% is prepared from 350 parts, by weight, of Polyol A and 100 parts, by weight, of 4,4'-diphenylmethane diisocyanate by stirring at 60° C.
  • the prepolymer is diluted with 150 parts, by weight, of butyl benzyl phthalate and 40 parts, by weight, of xylene and mixed with 200 parts, by weight, of furnace black.
  • tosyl isocyanate an auxiliary agent for improving the storage stability of the paste
  • 4 parts, by weight, of ⁇ -epoxypropyl-triethoxysilane (an auxiliary agent for improving adherence) and 0.6 parts, by weight, of dibutyl tin dilaurate (as catalyst) are added.
  • the composite material has a stability in storage of at least three months if moisture is excluded. At 23° C. and 50% relative humidity, the composite material forms a continuous skin within 30 minutes and hardness in about 3 days to a Shore hardness A of about 70.
  • the composite material manifests very good properties of adherence on glass.
  • the firm adherence is maintained even under exposure to UV light without requiring the aid of auxiliaries, such as black pigmented, special UV protective primers.
  • This example illustrates the high grade properties of a composite material according to the invention, especially the high stability under exposure to ultraviolet light and compares them to those of a conventional polyurethane.
  • Two liquids prepolymers having an isocyanate content of about 4% are prepared by the reaction of 400 parts, by weight, of Polyol A or Polyol C with, in each case, 100 parts, by weight, of 1-isocyanato-3,3,5-trimethyl-5-isocyanato methyl cyclohexane at 100° C. for 6 hours.
  • Two composite materials which have the following composition are prepared by mixing the resulting products with various additives:
  • Diisodecylphthalate 120 parts by weight
  • Both solvent-free composite materials remain workable for approximately one hour. When applied to window glass, they show good adherence after hardening one day. The surfaces of adherence between glass and composite material are exposed to a 300 Watt Vitalux lamp from a distance of 30 cm.
  • the composite material based on Polyol C can easily be detached from the surface of the glass after 200 hours exposure to light.
  • the composite material according to the invention based on Polyol A shows no change in its adherence after it has been exposed to light for 1000 hours.
  • the composite material is suitable for use in the construction of insulating glass.
  • This example illustrates the preparation of a moisture-hardening, low-solvent composite material which reacts with the aid of a latent hardener.
  • the prepolymer of Polyol A and 1-isocyanato-3,3,5-trimethyl-5-isocyanato-methylcyclohexane described in Example 4 is used.
  • the mixture of components forms a one-component sealing compound which may be stored for several months and when exposed to air at 23° C. and 50% relative humidity forms a continuous skin within 10 minutes and hardens to an elastic material.
  • This composite material is particularly suitable for sealing the expansion and connection joints in glass constructions.
  • a composite material according to the invention is compared with a polyurethane-based composite material which is not according to the invention.
  • the polyurethanes prepared in Example 6 are used for further investigations to demonstrate the advantages of the composite materials according to the invention.
  • the polyurethanes obtained from Polyol A and Polyol C are stored for 30 minutes at 180° C. and the change in properties is then tested.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Civil Engineering (AREA)
  • Structural Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Joining Of Glass To Other Materials (AREA)
  • Sealing Material Composition (AREA)
US06/454,520 1982-01-09 1982-12-30 Process for preparing glass constructions Expired - Lifetime US4433010A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3200430 1982-01-09
DE19823200430 DE3200430A1 (de) 1982-01-09 1982-01-09 Verwendung von ein- oder mehrkomponentensystemen als bzw. zur herstellung von verbundmassen fuer glaskonstruktionen

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US (1) US4433010A (de)
EP (1) EP0083797B1 (de)
JP (1) JPS58135159A (de)
AT (1) ATE12133T1 (de)
CA (1) CA1180237A (de)
DE (2) DE3200430A1 (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4810674A (en) * 1987-02-24 1989-03-07 Hoechst Celanese Corp. Porous glass monoliths
US4938521A (en) * 1987-09-10 1990-07-03 Saint Gobain Vitrage Spacer for vehicle windshield
US5057265A (en) * 1989-09-12 1991-10-15 Saint Gobain Vitrage International Method of making a spacer for a windshield bracket
US5095669A (en) * 1989-12-13 1992-03-17 Saint Gobain Vitrage International Spacer for windshield bracket
US5384995A (en) * 1989-09-12 1995-01-31 St. Gobain Vitrage International Spacer for windshield bracket
US5391416A (en) * 1991-01-11 1995-02-21 St. Gobain Vitrage International Glass pane assembly
US5574124A (en) * 1994-08-17 1996-11-12 Bayer Aktiengesellschaft Isocyanate prepolymers, a process for their preparation and their use
US5800861A (en) * 1985-08-15 1998-09-01 The Sherwin-Williams Company High solid infrared absorbing compositions
WO2014047018A3 (en) * 2012-09-19 2014-05-30 3M Innovative Properties Company Coating compositions and articles made therefrom
WO2014055578A3 (en) * 2012-10-03 2014-06-26 3M Innovative Properties Company Coating compositions and articles made therefrom

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GB8502959D0 (en) * 1985-02-06 1985-03-06 Bostik Ltd Multiple glazing
DE3536806A1 (de) * 1985-10-16 1987-04-16 Flachglas Ag Aggregat aus kraftfahrzeugscheibe und befestigungleiste
FR2594479B1 (fr) * 1986-02-20 1991-05-31 Saint Gobain Vitrage Vitrage multiple, procede d'obtention et dispositif pour la mise en oeuvre de ce procede
JP2674994B2 (ja) * 1986-02-20 1997-11-12 サン−ゴバン・ヴイトラ−ジユ 多層ガラス、その製造方法及び製造装置
JPS63245485A (ja) * 1987-03-31 1988-10-12 Sanyo Chem Ind Ltd 陶管シ−ル用プライマ−
JPH0520523Y2 (de) * 1987-11-18 1993-05-27
ES2047081T3 (es) * 1988-09-27 1994-02-16 Lingemann Helmut Gmbh & Co Separador para cristal aislante de varias lunas.
DE4229090A1 (de) * 1992-09-01 1994-03-03 Ver Glaswerke Gmbh Verfahren zur Herstellung einer Verbundglasscheibe mit einer umlaufenden Dichtlippe aus einem Polymer
DE4426744A1 (de) 1994-07-28 1996-02-01 Sekurit Saint Gobain Deutsch Höhenverstellbares Seitenfenster für Kraftfahrzeuge
ATE372226T1 (de) 2000-10-10 2007-09-15 Saint Gobain Verwendung von verglasung mit einem profiliertem band zu seiner installation in einer öffnung
DE102004054348A1 (de) * 2004-11-09 2006-05-11 Hsb Selbstbausysteme Gmbh Verfahren zur Herstellung eines Verbundglases und Verbundglas

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5800861A (en) * 1985-08-15 1998-09-01 The Sherwin-Williams Company High solid infrared absorbing compositions
US4810674A (en) * 1987-02-24 1989-03-07 Hoechst Celanese Corp. Porous glass monoliths
US4938521A (en) * 1987-09-10 1990-07-03 Saint Gobain Vitrage Spacer for vehicle windshield
USRE37395E1 (en) 1987-09-10 2001-10-02 Saint-Gobain Glass France Method of centering windshield glazings
US5519979A (en) * 1988-09-09 1996-05-28 Saint Gobain Vitrage Method of centering windshield glazings
US5057265A (en) * 1989-09-12 1991-10-15 Saint Gobain Vitrage International Method of making a spacer for a windshield bracket
US5384995A (en) * 1989-09-12 1995-01-31 St. Gobain Vitrage International Spacer for windshield bracket
US5095669A (en) * 1989-12-13 1992-03-17 Saint Gobain Vitrage International Spacer for windshield bracket
US5391416A (en) * 1991-01-11 1995-02-21 St. Gobain Vitrage International Glass pane assembly
US5574124A (en) * 1994-08-17 1996-11-12 Bayer Aktiengesellschaft Isocyanate prepolymers, a process for their preparation and their use
WO2014047018A3 (en) * 2012-09-19 2014-05-30 3M Innovative Properties Company Coating compositions and articles made therefrom
WO2014055578A3 (en) * 2012-10-03 2014-06-26 3M Innovative Properties Company Coating compositions and articles made therefrom

Also Published As

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CA1180237A (en) 1985-01-02
DE3200430A1 (de) 1983-07-21
DE3262577D1 (en) 1985-04-18
ATE12133T1 (de) 1985-03-15
JPS58135159A (ja) 1983-08-11
EP0083797B1 (de) 1985-03-13
EP0083797A1 (de) 1983-07-20

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